There might be something amiss in my cognitive development as it seems that from my years of being a toddler until now, my favorite books to read are those with pictures in them. One has been getting me quite inspired as of late: 100 Years of Menswear by Cally Blackman. I particularly enjoyed the pages on the years around the early 20th century—forward thinking as we all strive to be today, it is always good practice to master the classics.

The world’s first male style icon, Edward Prince of Wales, shows men how to accessorize: with a hat, a full beard, a nosegay, a cane, and heeled shoes.

The book got me pondering on the question “What is progressive?” Comme des Garcons constantly references old old menswear and tweaks the proportions to their signature delightful unflattery, and, top of mind, Balenciaga womenswear Fall 2007, a collection that I found strikingly progressive and conceptual, was in essence a mishmash of references from the past: striped tennis blazers, military jodphurs, all topped off with then-controversial Arabic scarves. If you think about it, what boldness did the trendsetters of yesteryears have, without any trend-dictating fashion houses available to men, these guys had merely ideas of how they wanted to dress, and they would come to their tailors telling them to do this and that, starting a revolution wearing their new duds on the street. Now that’s progressive.

On the left, a gentleman wears oxford bags, a flamboyant sign of rebellion against mainstream fashion, popularized by a group of Oxford University undergrads. On the right, Cambridge undergraduates set the trend of wearing plus-fours in the city, these baggy short trousers once only worn when hunting.

The book elaborates on the classic male archetypes—the aristocrat, the working man, the student, the athlete, the artist—and how each of these have had an imprint on what it is to be a man today and how they have influenced what we wear.

Tsuguharu Foujita, a Japanese artist living in Paris in the 1920s, wears a floral band-collar shirt with an even busier plaid cardigan, topped off with a salt-and-pepper bowl cut and round glasses. This reminds me a lot of what I wear today. Weird never goes out of style.

Times of war forced clothing manufacturers to be pragmatic and utilitarian. On the right page, upper left shows a practical, inexpensively made plaid flannel jumpsuit, and on the right, a suit made without lapels or pocket flaps—features that were considered superfluous at the time. That lapel-less jacket wouldn’t be out of place at a Damir Doma or Siki Im show today.

Labor Day Weekend will be me, a glass of spiked whole milk, PB&J’s, and my two new picture books: 100 Years of Menswear (as featured above), and for further, forward-looking reading, 100 New Fashion Designers (with favorites Erdem, Peter Pilotto, and Tim Hamilton, among many others), both published by Laurence King